


Topsy Turvy

by Zeahart03



Category: Superjail! (Cartoon)
Genre: Best Friends, F/M, Friends to Lovers
Language: English
Status: In-Progress
Published: 2020-08-01
Updated: 2020-08-01
Packaged: 2021-03-06 05:06:57
Rating: Mature
Warnings: Graphic Depictions Of Violence, Major Character Death
Chapters: 2
Words: 2,637
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25657891
Author URL: https://archiveofourown.org/users/Zeahart03/pseuds/Zeahart03
Summary: Penny Rossi was normal lawyer always after on her father's ass about getting in line. One day, her father gets kidnapped by some flying robot in the sky. She hitches a ride from the back of the robot, but finds herself in some kind of odd dimension? Will she can she be able to return home with her father? And, whose idea was it to make such a complicated jail anyway?
Relationships: Charise/Jared (Superjail!), The Warden (Superjail!)/Original Character(s), The Warden (Superjail!)/Other(s), The Warden (Superjail!)/You
Comments: 2
Kudos: 10





	1. Chapter 1

_Ring_

_Ring_

_Ring_

_You have one new voicemail_.

"Hey, uhh, peanut. It's Daddy. I need your help again, I'm in a bit of a predicament, and I need your help. Daddy's friend, Welch, got into some bad shit. Call me back when you can. Love you." 

_End of Message_

The woman rolled her eyes. In her hand, was a cigarette that wasn't lit. The other had a cellphone that was flipped up to read messages. Penelope Rossi thought it was a good idea to take her break early, but unfortunately, her father just had to always get himself into some kind of legal trouble.

It was a common occurence. Her father had been arrested for 76 times already. He always had the same excuse that 'he was caught up in the moment'. This time was no different.

Penny was a beginner at law. At night she studied to get her law degree, while during the day, she was a waitress at a local bar. Most of the time, she was worried about her father, and what kind of trouble he would get himself into.

Despite all the fuss, Penny could help him out, even when he didn't help her out.

Wheeling out of the courtroom, her father had a huge grin on her face. 

"Thanks a lot, Peanut!! I owe ya one." He said, smiling at his daughter.

Penny didn't smile back. 

"I just can't believe it, that's the 5th traffic violation this month." Penny yelled. "Welch can't even drive for God's sakes."

"I've got no one else to drive me."

"Then, don't drive. You've been retired for 14 years now."

"Peanut", her father said, calmly. "You've got to understand that I run a business that I can't retire from. And, that business is called 'Life'."

"But, you won't be live any longer if you don't stop doing shit like this." Penny crossed her arms and sighed.

"Don't worry about me, sweetie. Just worry about you. You've got you're whole life ahead of ya."

"Dad," Penny took a deep breath, "listen to me. You can't keep doing this. Please tell me, you'll at least try to stay out of trouble."

"I swear to you, Peanut. I will never break any laws again."

"No, Dad-" Penny pulled her father close to her to the point where her glasses touched his. "You have to promise me. PLEASE."

"Alright, alright. Jesus, kid. I promise." Her father crossed a 'T' around his chest. "Can we get going? Seinfeld comes on at 8."

Penny sighed wheeling her father to the car. 

Just as Penny was unlocking the car, the clouds began to darken as if it was going to rain. Instead, a giant robot came emerging from the clouds. The robot took Penny's father by the handles of his wheelchair.

"AHH PENNYYY!!" Her father screamed.

Penny stood by her car, speechless. "Are you fucking kidding me?" She whispered to herself.

This was an absolute nightmare.

  
The next day came around like nothing happened. Penny walked into the police station, with hope that they could help.

"So, your father was abducted by a flying robot from the sky?" The officer said, in a dreary voice.

"I know that might seem crazy, but I really got to find him, sir." Penny said, trying to sound as helpless as possible. Penny's father didn't have that good of a relationship with the local police department. It seemed that everyone knew how much of a pain in the ass he is. Despite that, Penny was determined to find him.

"Listen, lady, it just seems that maybe your dad went to a better place. After all, we wouldn't know were to find any flying robots." The police officer chuckled.

Penny glared. "Well, thank you for at least trying." She walked out of the building, and lit a cigarette. As the cigarette was burning, Penny couldn't help but stare at the failure of actually trying to quit the habit. "Lazy bastards."

Next to her, a strange mullet wearing man seemed to be mumbling something.

Penny just rolled her eyes. He was either making fun of her appearance or her clothing. Most people do that. A short stubby woman is easy to pick on for some people, but Penny didn't have time to deal with shit like this.

She decided to ignore him, putting out the cigarette.

Suddenly, the dude pulled a knife out on Penny, and held close to her throat. She glared, jamming her heels into his balls.

The guy in the mullet whimpered, and fell to the ground. As he fell to the ground, the clouds began to darken again.

The robot came flying down, grabbed the now injured mullet guy by his foot, and turned around to fly up back into the clouds.

Penny saw this opportunity to jump on the robot's back as it was flying off. While doing so, her heel fell off.

"MY EYE-" Someone said.

Penny was more focused on staying on the robot. The clouds seemed to appear in the shape of a mans face, 'swallowing' the robot before disappearing completely.

The robot, then, dropped the man into some kind of garbage chute.

Penny seemed to be sliding off the edges of the robot, but maintained her composure.

"Well done, Jailbot! That's two new prisoners in one day." A man's voice said. 

"Uhh, sir? We do have a problem with over population." Another man's voice said.

"That's not a problem, Jared. We have the local brawler pit on Wednesdays."

"Yes, but, sir-" Just as the man began to speak, Penny fell from the back of the robot. The robot jerked its body around, and glared at Penny. The robot used its extended arms to grab her. Penny huffed, feeling useless in the mechanical arms.

The robot brought Penny over to the two men that were talking before.

The man in the purple top hat had an enormous grin on his face. He almost looked like the Mad Hatter. Meanwhile, the stubby man next to him looked a bit confused.

"Why, who are you, my little stowaway?" The man smiled, pinching Penny's cheek slightly. 

Penny winced, slightly. "I'd really appreciate if you didn't do that. And, could you tell your robot to let me go?"

The man nodded, gesturing to the robot to put her down.

"Uhh, thanks. Anyways, what the hell is this place?"

The man seemed to get a glint of cheer in his eye. "This is Superjail, and I am the Warden. Superjail is far superior to all the other jails you've encountered in your life. The real world isn't ready for my methods of extremity. I'd be happy to give you a tour."

The Warden took his hat off and bowed. 

Penny smiled, slightly nervous. "Uhh, yeah, listen. I'm just looking for my dad."

"Your father's here? Why didn't you say so? I'm afraid visiting hours are over."

"No, I'm not here to visit. I'm a lawyer."

The Warden quirked an eyebrow. "A lawyer?"

"Sir," the short man said, "If there's a lawyer present, we're contractually obligated to let the lawyer see their client."

The Warden thought for a second. "Well, you did come all this way here. Sure, why not?"

Penny sighed in relief. "Great."

A strange car shaped like the face of the Warden appeared.

"Care for a ride?" The Warden said, opening the door for her.

Penny smiled, slightly, getting into the bizarre buggy.

"Before we begin our little tour, do you mind telling us your name?"

Penny looked back at the Warden, and nodded. "Call me, Penny."


	2. Chapter 2

"-and next to the cafeteria is the cellblocks." The Warden said, cheerfully as the buggy rode throughout Superjail.

The tour of the jail felt unreal. Every single ounce of this place seemed to have some kind of weird magical element. 

Penny felt so taken aback by everything. "Uhh, Mr. Warden, if you don't mind me asking, how do you find your criminals?" 

"I'm glad you asked. You see, I only seek out the biggest and baddest criminals. Criminals who've been tainted since birth to live a life of sin. I've dedicated my whole life to this tremendous prison, to uphold my father's legacy." The Warden seemed very pleased with himself in that speech.

"Well, I can assure you that might be a mistake. My father isn't that bad." Penny said, looking worried.

"Superjail makes no mistakes, dear." 

Penny thought for second. Whilst Jared looked up at the Warden with a worried look on his face. 

"Sir, there's lots of room for error in Jailbot, maybe if we-"

"Quiet, Jared, the young lady is trying to think."

After a while, they ended up at Penny's father's jail cell.

"Oh, Peanut, thank goodness you're here. I've been missing out on Seinfeld for the past two days." Her father hugged her through the bars. "Please get me out of here."

Penny turned to the Warden. "Could you give us a moment alone please?"

The Warden nodded. "Take ask much time as you like." He left with Jared following behind.

  
The Warden sat up in his office, leaning back in his chair with a somewhat dreamy look on his face. "Isn't it great, Jared? A woman like that can hardly be found in Superjail. So refined and polite. She's perfect."

"Yes, but, uhh, sir, you also locked up her father." Jared stated. "F-from my knowledge, ladies think it's rude to kidnap their father."

The Warden nodded. "But, how else would we come together?" The Warden took out a pair of binoculars. He saw Penny speaking with her father, somewhat curious about what they were saying. He saw her tired face. She looked hopeless, desperately trying to talk to her father about important matters.

"That's it!" The Warden snapped his fingers. "We'll give them their very own trial here in Superjail!"

"But, sir, a trial, just for them. What about the other prisoners?"

"They'll be the jury, and determine the fate of Ms. Penny, and Mr. Rossi." The Warden smiled at his brilliant plan.

"I'll plan it at once." Jared scurried out of the Warden's office.

  
Penny sat in the cafeteria next to her father who was complaining about the prison food.

To Penny's surprise, a big burly woman appeared from the entrance of the cafeteria, wearing a police uniform, and seemed to punch everyone that got in her way. Penny felt intimidated by her presence, but continued to eat what garbage was left on her plate.

The woman walked up to Penny, and tapped her on the shoulder. The woman lingering shadow loomed over Penny, as the woman began to speak.

"Hey," the woman said, in a surprisingly deep voice. "The Warden would like a word with you."

"Yes, of course." Penny got up from her seat, and carried her father in his wheelchair. 

"Would you mind telling me who you are?"

"The name's Alice. I'm a guard here. This entire place is like a sausage fest." The woman said, as she led Penny to the elevator.

"Yeah, there's a lot of men here."

"Let me tell you, sister. You better watch your back. The guys here crave fresh meat."

Penny rolled her eyes. "I've heard it all before."

"But, you've never been in a jail like this, hun." 

Penny sighed. Alice was right. This jail seemed like a different dimension. It was almost impressive. Penny's thoughts were interrupted by the sound of the elevator stopping.

"Here's your floor." Alice said, before closing the elevator behind Penny.

"Ah, Penny! Hello! Are you enjoying Superjail?" The Warden pulled Penny into a hug. 

Penny smiled, nervously. "Well, it's pretty impressive, Mr. Warden."

"Oh, please. Enough with the formalities. Just call me Warden." The Warden said.

Her father glared at him. "Listen, buddy, now that I have my lawyer present, I demand a trial."

"Of course, Mr. Rossi. I was thinking the same thing." The Warden pulled Penny's father close to his ear. "We'll set the trial on a huge screen, whereas you will be judged by the denizens of Superjail, then I, the judge, will determine you're fate."

The Warden transformed the office into a giant courtroom. The Warden appears on a podium wearing a powered wig with long black rooms. Jared stood next to him, as the prosecutor, while trying to get all the paperwork together.

"Just a second." Jared said. "I only studied a little bit of law while I was in college, so bare with me here."

Jared stood in front of the Warden, and pointed towards Penny's father.

"Mr. Rossi has been convicted of the following: burglary, drug dealing, possession of drugs, 2nd degree murder, embezzlement, prostitution.." Jared continued listing all Mr. Rossi's offenses for about 30 minutes.

The entire time, Penny had her head on the desk. 

"Ms. Rossi, make your case." The Warden said, banging his gravel.

Penny stood up, and cleared her throat. "Yes, well, Mr. Rossi is innocent of all these claims. You see, he's a very old disabled man, and needs a wheelchair to get around, that's why it's mostly impossible to claim, such charges."

"Good point, he is in a wheelchair." Jared said. "But, your honor, he still could've done the following: prostitution, embezzlement, burglary, etc."

"Mmm, I see." The Warden said. He had his eyes fixated on Penny. She already seemed so defeated. 

After many rebuttals and discussions, the Warden called in a recess.

He walked up to Penny, who was rereading papers that were laid out on the desk. The Warden tried to strike up a conversation with her, but everytime he was brought down by her saying that she's busy.

Mr. Rossi watched the Warden's movements as he tried to woo Penny. It got him thinking. He tapped the Warden on the shoulder.

"Hey, eggplant." Mr. Rossi said.

The Warden turned around and crossed his arms. "Listen, if this has anything to do with the trial, then I'll automatically count you as guilty."

"Actually, it's about my daughter. She's been pretty bummed out about the whole situation." Mr. Rossi smirked. "And, when she doesn't have her nose stuck in paperwork, she's actually a swell gal. It would be a shame if she were to leave, huh?"

The Warden thought for a second. "Yeah, I want to get to know her more. There hasn't been a new fresh face in Superjail in over a decade. I see potential in her as a new guard."

"What if I were to convince her to stay?" Mr. Rossi shrugged. "In exchange, I leave this place free of charge? What ya say, eggplant?"

The Warden nodded. "Mmmm, alright you've got a deal!"

The Warden put back on his powered wig, and banged the gavel, getting everyone's attention. 

"I, the Judge of Superjail, hereby say Mr. Rossi is not guilty!"

Everyone in the room looked incredibly confused. 

Jared started sweating. "But, sir, Mr. Rossi has so many charges that he'd have to say here for 167 years."

"Well, Jared, he's shown a sign of honesty. He admitted to those crimes, and under Superjail oath, he is found not guilty." The Warden beamed. 

Penny looked baffled, while her father was smirking up at the Warden. 

"Uhh, Dad," Penny whispered, "what did you discuss with the Warden during recess?"

"Oh, I just said that he could keep you, if I could leave."

"YOU WHAT-" Penny screamed, but her father muffled her with his hand.

"Quiet, peanut. You'll be ok." 

Penny glared. "You're an asshole. Just trading me off like I'm some pawn in your little game. You always do some shit like this, and I'm always the on responsible for your messes. When the hell will you learn the consequences for your goddamn actions!!"

Her father wasn't listening. Jailbot had already grabbed ahold of his wheelchair, and flew off, leaving Penny stranded in this strange place called Superjail.


End file.
